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Cleveland, Wisconsin, United States of America

Cleveland vacation rentals

We found 52 vacation rentals — enter your dates for availability

Discover a selection of 52 vacation rentals in Cleveland, WI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $150 per night, and houses and condos are popular options for a stay in Cleveland. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Cleveland

Amazing Lake Views, easily accessible and close to Whistling Straits

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$338 avg/night
(50)

Golf and Lake Get-a-Way near Sheboy/Elkhart Lake/Whistling Straits-WINTER RATES!

Sleeps 6 · 1 Bedroom · 1 Bathroom
$150 avg/night
(16)

Lake Michigan Retreat in Cleveland WI - Great place - Great Lake

Sleeps 7 · 3 Bedrooms · 2 Bathrooms
$167 avg/night

Luxury and relaxation on 5 private acres and 300' beach on Lake Michigan

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
$445 avg/night
(38)

Tranquil, private lake view Villa - Hika Bay Haven

Sleeps 7 · 3 Bedrooms · 2 Bathrooms
$523 avg/night

3 mins from Ryder

Sleeps 4 · 1 Bedroom
$3,000 avg/night

Search 52 vacation rentals

Top rated rentals — Cleveland
Stayed Apr 2022

Wonderful Home - Lived up to Every Expectation!

We loved staying in this home, and will be back the next time we are in Manitowoc. It was extra clean when we arrived, had everything we needed for our stay, and the owners were terrific to work with. The basement was awesome to hang out in, and the ...

Jeffrey B.
Jeffrey B.
Stayed Apr 2022

Great views, very comfortable.

Our family of all ages (16 to 91) was comfortable at this lakefront home. The views from many rooms were wonderful. Sunrise and moonset, birds and wild turkeys. There are quite a few stairs to the living room from the entry level, but worth the climb...

Claire S.
Claire S.

Wilmette

Stayed Feb 2022

Relaxing Winter Getaway

What a fun trip! Monika and her team were really easy to work with and the property was amazing! The home is recently renovated and has three main sections where a family could easily sleep. We had a family of 4 and we could have easily fit another f...

Krystian M.
Krystian M.
Stayed Feb 2022

Fabulous house for a family gathering!

We came up from St Louis with family for my father-in-laws 90th birthday party over in nearby Plymouth. We had 6 total adults and 3 kids, so more than enough sleeping space for everyone. The grandkids enjoyed the legos and Lincoln logs that were avai...

Elise F.
Elise F.
Stayed Feb 2022

Nice, quiet weekend getaway

We had a relaxing 3 day weekend stay here. The cabin was clean, cozy, and fairly well-stocked. We appreciated that there was plenty of firewood available to build a fire outside. Not too much to do in the winter with the lake being frozen over, but i...

Alexis I.
Alexis I.
Stayed Dec 2021

Great winter get away with the family.

Our family needed a change of scenery during another Covid spike. The property felt very welcoming and clean. Even though it was incredibly cold while we were there, the enormous windows gave us the feeling of being outside and enjoying the outdoors....

Colin M.
Colin M.

Evanston IL

Stayed Dec 2021

Great place.

This was our second time we’ve rented this property. Great location with awesome views and sounds of Lake Michigan. We’ve stayed in the off season (November and December) when Lake Michigan has been roiling. There is nothing like reading a book or ly...

Mark M.
Mark M.
Stayed Nov 2021

good and bad

Property is spectacular, communication with the person that was on VRBO - bad, had he answered the questions I sent him then we would have been better prepared. Description of beds on site is wrong - not knowing what floors they were on is not good. ...

Cynthia M.
Cynthia M.
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How many vacation rentals are available around Cleveland, WI?

Our 2022 property listings offer a large selection of 52 vacation rentals around Cleveland. From 47 house rentals to 2 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Cleveland?

Yes, of course. Vrbo has 47 Houses in Cleveland. Our other popular types of vacation rentals in Cleveland include:

  • Condos/Apartments: 2 rentals available
  • Cabins: 4 rentals available
  • Cottages: 4 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Studios and more.

Can I find a vacation rental with pool in Cleveland?

Yes, you can select your preferred vacation rental with pool among our 3 vacation rentals with pool available in Cleveland. Please use our search bar to access the selection of vacation rentals available.